Apartments in Province of Siena and Villas – Holiday Lettings - Holiday Rentals Province of Siena

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4,162 Holiday homes

(30) Excellent 

1 / 25

Tuscan apartment in rural setting with easy access to nearby cities, property has private garden and shared pool

San Gimignano / Castel San Gimignano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
The apartment is located in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the oliv  …see more

from £84 / night

£459 - £709 / week

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from £84 / night

(40) Excellent 

1 / 19

Stunning farmhouse apartment located between Tuscan cities of San Gimignano and Volterra, shared pool, private garden, sleeps 6

Province of Siena / San Gimignano

3 bedroomsSleeps 64 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Car essential;
Azzurra is an apartment in Poderra Torrichi, a gated community of three farm buildings, which is located between the medieval cities of San Gimignano and Volterra. Podera Torrichi is newly renovated and has retained the charm of the traditional Tuscan farm buildings, wi  …see more

from £184 / night

£993 - £1451 / week

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from £184 / night

(18) Excellent 

1 / 49

3 bedroom holiday apartment near Tuscan cities, staffed property with outdoor pool

San Gimignano / Castel San Gimignano

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
The apartment is placed in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the olive  …see more

from £84 / night

£459 - £709 / week

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from £84 / night

(2) Excellent 

1 / 18

Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 27 nights min stay

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Pets welcome;
 …see more

from £75 / night

£525 - £800 / week

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from £75 / night

(1) Excellent 

1 / 14

New Casa Titta apt 3 bedrooms , amazing view

San Gimignano / Castel San Gimignano

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 55 km; Great for children of all ages ; Car advised;
C asa Titta is our third apartment ,completely new ,really comfortable, placed on the first floor with three bedrooms for 5 people and a large open space living . A new kitchen equipped with dishwasher , fridge/freezer, microwave and electrical hoven. The bathroom has  …see more

from £84 / night

£459 - £709 / week

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from £84 / night

1 / 24

Province of Siena / Pienza

1 bedroomSleeps 35 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 5 nights min stay
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
 …see more

from £105 / night

£0 / week

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from £105 / night

1 / 31

Villa Colombaio - Asciano villa sleeps 9

Province of Siena / Asciano

5 bedroomsSleeps 9Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
As guests enter the property there is an entrance hall leading off to a living area on the right and large kitchen on the left. This area has an open plan feel to it. The kitchen is superbly equipped with everything guests could possibly need and want during their stay.  …see more

from £233 / night

£1625 - £3500 / week

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from £233 / night

(11) Excellent 

1 / 21

charming cottage in peaceful country setting

Montepulciano / Gracciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 90 km; Swimming pool; Great for children of all ages ;
The cottage is opposite the owner's house and consists of two double bedrooms, two bathrooms and a large living room with cooking area. The living area opens onto a patio and pergola and the downstairs bedroom also opens onto a small patio. There is access for the disa  …see more

from £67 / night

£384 - £1717 / week

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from £67 / night

(6) Excellent 

1 / 24

Province of Siena / San Gimignano

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 70 km; Great for children of all ages ; Car advised;
 …see more

from £92 / night

£584 - £700 / week

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from £92 / night

1 / 15

35827-Apartment Montepulciano - Abbadia di Montepulciano apartment sleeps 4

Montepulciano / Abbadia di Montepulciano

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
Elegant house restored in the second half of the 1800s. It is situated in a property of approximately 12 hectares where there are olive trees and a vineyard from which an excellent Chianti wine (D.O.C.G.) and the famous Nobile di Montepulciano (D.O.C.G.) wine are made.  …see more

from £102 / night

£710 - £1050 / week

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from £102 / night

1 / 28

Holiday lodging near Pienza P5 - Torrita di Siena apartment sleeps 5

Province of Siena / Torrita di Siena

1 bedroomSleeps 57 nights min stay

  • 1 bedroom
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
This lovely country house with pool in Tuscany is located at 1.5km from the beautiful medieval village of Torrita di Siena, in the heart of Val di Chiana, only 15 km from Pienza and Montepulciano, and 48 km from Siena. Situated on a knoll, the 18th-century farmhouse is  …see more

from £44 / night

£305 - £575 / week

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from £44 / night

1 / 16

Castle Cottage (v011) - San Casciano dei Bagni cottage sleeps 6

Province of Siena / San Casciano dei Bagni

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 40 km; Swimming pool; Great for children of all ages ;
The cottage is in the heart of the hamlet which is completely surrounded by ancient walls, and has a splendid view of the parish church and all the valley. It is independent and surrounded by a large garden. All the ceramics in the house were painted by the owner and ha  …see more

from £118 / night

£825 - £1059 / week

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from £118 / night

(9) Very Good 

1 / 31

Le Fontanelle - rustic farm buildings with pool

Province of Siena / San Gimignano

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
Nestled in a centuries-old complex of farm-house buildings, just 10 minutes drive from the medieval "skyscraper" fortress town of San Gimignano...Le Fontanelle is the perfect place to soak in Tuscany's sunshine, culture, food and fun.An easy drive from Pi  …see more

from £96 / night

£596 - £788 / week

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from £96 / night

1 / 100

Belle Viste - Belle Viste - Guazzino apartment sleeps 2

Sinalunga / Guazzino

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Nearest beach 0.3 km; Great for children of all ages ; No pets allowed;
ExteriorsThe apartment is located on the second floor of a XIX century building in a small village in south Tuscany. Restaurants, Shops and Bars are at walking distance. The apartment offers a free parking space just in front of the building. High way A1 and Free Way Si  …see more

from £43 / night

£298 - £309 / week

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from £43 / night

1 / 22

Holiday Apartments near Pienza - Torrita di Siena farmhouse sleeps 3

Province of Siena / Torrita di Siena

1 bedroomSleeps 37 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
This lovely country house with pool in Tuscany is located at 1.5km from the beautiful medieval village of Torrita di Siena, in the heart of Val di Chiana, only 15 km from Pienza and Montepulciano, and 48 km from Siena. Situated on a knoll, the 18th-century farmhouse is  …see more

from £34 / night

£234 - £492 / week

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from £34 / night

1 / 36

Villa Le Crete - Castelmuzio villa sleeps 6

Province of Siena / Castelmuzio

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
This little, two-storey, converted Tuscany farmhouse has been meticulously restored in a simple, rustic style, employing high-quality traditional materials. Set on a gentle elevation in a remote spot, it is entirely surrounded by the clay hills called “Crete Senesi”  …see more

from £150 / night

£875 - £1250 / week

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from £150 / night

1 / 20

Villa Olmo - Radicofani villa sleeps 14

Province of Siena / Radicofani

7 bedroomsSleeps 147 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
The villa lies in a hilly location with stunning panoramic views of the surrounding hills and mountains, about 8 km from the village of Radicofani. It is an ideal starting point for enjoying the tranquility of the surrounding mountainous landscape and on the other to ma  …see more

from £417 / night

£1667 - £2917 / week

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from £417 / night

(21) Excellent 

1 / 29

San Gimignano / Pancole

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 90 km; Great for children of all ages ; Car essential;
 …see more

from £46 / night

£280 - £405 / week

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from £46 / night

1 / 12

Province of Siena / San Quirico d'Orcia

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £66 / night

£421 - £607 / week

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from £66 / night

(3) Excellent 

1 / 33

Province of Siena / Murlo

2 bedroomsSleeps 52 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
 …see more

from £67 / night

£459 - £542 / week

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from £67 / night

(32) Excellent 

1 / 24

1 bedroom luxury apartment with Private Garden, Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Car advised;
Surrounded by the famous rolling hills covered with vineyards and olive groves, which give the name to some of the most prestigious Chianti wine is Borgo di Gaiole. The apartment is on the ground floor as you enter the Borgo, private and self contained around 60sq meter  …see more

from £90 / night

£630 - £770 / week

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from £90 / night

1 / 100

Castellina - small - Castellina In Chianti apartment sleeps 2

Province of Siena / Castellina In Chianti

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
These apartments are ideal for a romantic escape in Tuscany. Both apartments comes with fire burning fireplace, a small but refined living room with sofa bed an equipped kitchenette and a double king size bedroom and bathroom with shower. Both apartments have windows op  …see more

from £95 / night

£665 - £940 / week

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from £95 / night

(7) Excellent 

1 / 18

3 bedroom farmhouse in the picturesque Tuscan hills boasting private pool, terrace and garden, sleeps 6

Province of Siena / San Gimignano

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 45 km; Swimming pool; Great for children of all ages ;
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from £82 / night

£550 - £1042 / week

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from £82 / night

1 / 11

Torrita di Siena flats O - Torrita di Siena apartment sleeps 3

Province of Siena / Torrita di Siena

1 bedroomSleeps 33 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Great for children of all ages ; Car advised; No pets allowed;
This beautiful holiday home is located at 200 mt from the pretty medieval village of Torrita di Siena, only 15 km from Pienza and Montepulciano, in the heart of Val di Chiana, an attractive valley in the south-east of the region. The farmhouse faces on a side the villag  …see more

from £60 / night

£200 - £388 / week

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from £60 / night

(28) Excellent 

1 / 20

Amazing Tuscan holiday apartment in the historical Town centre of Colle di Val d'Elsa, sleeps 4

Province of Siena / Colle di Val d'Elsa

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 50 km; Great for children of all ages ; Car advised;
The Dietro Le Mura holiday home has been completely renovated and is located in the historical town centre of Colle di Val d'Elsa, a characteristically medieval town steeped in history. The apartment is on the first floor, has its own entrance and possible parking  …see more

from £67 / night

£450 - £559 / week

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from £67 / night

1 / 48

La Grancia Country Resort Apt4 - Montisi fort sleeps 3

Province of Siena / Montisi

1 bedroomSleeps 33 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
La Grancia Country Resort is a romantic and charming 14th century fortress used as a "Grancia", a granary for the storage of the produce grown on the property. Perched next to the delightful hilltop village of Montisi, it overlooks the surrounding Tuscany coun  …see more

from £104 / night

£715 - £794 / week

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from £104 / night

1 / 12

35781-Apartment Chiusi - Chian - Cetona apartment sleeps 2

Province of Siena / Cetona

1 bedroomSleeps 27 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Great for children of all ages ; Car not necessary; Pets welcome;
17th century 'Borgo' overlooking the Val d'Orcia, consisting of 15 living units, amongst which some<br>apartments and some suites. The 'Borgo' includes a marvellous garden with a large variety of plants,<br>fruit trees, flowers and h  …see more

from £78 / night

£543 - £821 / week

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from £78 / night

(7) Excellent 

1 / 41

Unique, charming farmhouse in Tuscany countryside with shared outdoor pool, sleeps up to 6

Province of Siena / Montepulciano

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 0 km; Swimming pool; Great for children of all ages ;
The main arched entrance leads past a utility room and downstairs bathroom into the open plan kitchen and dining room with dining table for 6 guests. The lounge has two sofa's one of which is a comfortable double sofa bed There is a wood burning stove in the lounge  …see more

from £72 / night

£500 - £890 / week

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from £72 / night

(3) Excellent 

1 / 35

Province of Siena / San Gimignano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Great for children of all ages ;
 …see more

from £84 / night

£525 - £875 / week

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from £84 / night

(6) Very Good 

1 / 18

Holiday apartment in restored Tuscan farmhouse, sleeps 4, features private garden and shared pool

Province of Siena / San Gimignano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
'Podere Torricchi' is a small collection of renovated 16th Century farm buildings converted into luxury houses and apartments. 'Torricchi 6' is a beautiful spacious ground floor house and is located on a hill with stunning views of the Tuscan hills. The renovation has r  …see more

from £75 / night

£525 - £800 / week

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from £75 / night

(3) Excellent 

1 / 31

Agriturismo Sammonti - Monteriggioni farmhouse sleeps 2

Province of Siena / Monteriggioni

1 bedroomSleeps 22 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
The “borgo Sammonti” was built in the beginning of the 13th century as a fortress in the county of Scorgiano, and it is located near most beautiful and important tuscan cities. The structure is surrounded by woods and it offers many paths for walks and escursions.T  …see more

from £63 / night

£417 - £625 / week

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from £63 / night

1 / 19

Fern Cottage (v044) - Cetona cottage sleeps 10

Province of Siena / Cetona

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
This charming cottage is made up of a kitchen, a living room with fireplace, a dining room, a study, a guest bathroom and a double bedroom with en-suite bathroom with shower on the ground floor. On the first floor there is a double bedroom with en-suite with shower,  …see more

from £314 / night

£2192 - £3092 / week

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from £314 / night

(6) Excellent 

1 / 10

Province of Siena / Sovicille

2 bedroomsSleeps 52 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Nearest beach 72 km; Swimming pool; Great for children of all ages ;
 …see more

from £38 / night

£467 - £2100 / week

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from £38 / night

(40) Excellent 

1 / 25

Lovingly restored stone-built Tuscan barn

Province of Siena / San Gimignano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
Podere Torricchi is a small collection of beautifully renovated 16th Century farm buildings converted into houses and apartments. Set on a hill the entire site has stunning views of the rolling Tuscan countryside. I'l Granario' is a house set on two floors, tastefully r  …see more

from £90 / night

£625 - £925 / week

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from £90 / night

(5) Very Good 

1 / 49

La Grancia Country Resort Apt1 - Montisi fort sleeps 3

Province of Siena / Montisi

1 bedroomSleeps 33 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
La Grancia Country Resort is a romantic and charming 14th century fortress used as a "Grancia", a granary for the storage of the produce grown on the property. Perched next to the delightful hilltop village of Montisi, it overlooks the surrounding Tuscany coun  …see more

from £104 / night

£715 - £794 / week

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from £104 / night

(7) Very Good 

1 / 5

TuscanFlat - Siena apartment sleeps 4

Province of Siena / Siena

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 105 km; Not suitable for children; Car not necessary;
This very stylish 430-square-foot apartment a few minutes walk from Piazza del Campo.You will need to walk up 66 steps to access this apartment, but the effort is amply rewarded by two amazing terraces and their spectacular views. The main living space here is a large,  …see more

from £84 / night

£642 - £1250 / week

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from £84 / night

(3) Excellent 

1 / 25

Province of Siena / Vivo d'Orcia

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 70 km; Ski; Great for children of all ages ;
 …see more

from £59 / night

£375 / week

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from £59 / night

(3) Excellent 

1 / 44

I MELOGRANI I:5 BDR Tuscan villa,view,pool ,WiFi

Province of Siena / San Giovanni d'Asso

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
You could not ask for a more special place in which to celebrate an important anniversary or simply spend a vacation with your family and friends ! I Melograni is a beautiful antique,indipendent, "casale" with large swimming pool (5x12 sqm), 1km away (walking distance!  …see more

from £452 / night

£3167 - £4084 / week

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from £452 / night

(21) Excellent 

1 / 18

Elegant 2 bedroom apt. in historic Siena residence

Province of Siena / Siena

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Great for children of all ages ; Car not necessary; No pets allowed;
Historic Residence Palazzo Bichi Ruspoli is situated on the main street, in the heart of Siena. The entrance is from the ancient tower, one of the three buildings wich the palace is composed. The house is on the third floor with elevator and has a stunning view on the c  …see more

from £134 / night

£867 - £2063 / week

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from £134 / night

1 / 10

STALLINA - Siena apartment sleeps 2

1 bedroomSleeps 22 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Great for children of all ages ; Pets welcome; Private garden;
The apartment is named STALLINA (small barn) and it is a cosy studio apartment forming part of the building of the "SCUDERIA" (stable) with a separate entrance and direct access from the garden. The studio has a living room with sofa bed, kitchenette and bathroom with s  …see more

from £43 / night

£269 / week

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from £43 / night

Top Destination reviews

COSOLI CHARMING HISTORICAL VILLA IN CHIANTI
Tuscan Heaven

Cosoli is a beautiful villa in a stunning location. It was a superb family holiday location. thanks. … see more
Pink Holiday-apartment with pool in Chianti
Wanderful stayin

The location of the house is in a very typical Tuscan environment: hills, vineyards, olive trees. Even if you might thing to be in a faraway place, the location is very convenient to Siena, San Giminiano, Firenze, and to other spots, such as Pisa an … see more
La Chiesina
An awesome villa in the Tuscan hills

A wonderfully restored church with plenty of character. Privacy with trees and hedges. Fab and accessible pool. Well equipped kitchen. An amazing welcome pack. We cycled from here to San Gimignano and to Monteriggioni. The location is superb and we d … see more
6 bedroom villa Tuscany (BFY13480)
excellent place, very ingoibale holliday

we stay in the villa for 5 nights. 5 couples 3 infants. everything was like it describe in the site. very large rooms with all the facilities you need. wifi works perfect, the pool was very clean. the kitchen was well equipped, the dining room ver … see more
Il Giardino
lovely and peaceful

Il Giardino is a wonderful, intimate place. The house is not huge - but it is perfect for a family.The outside space is so beautiful and serene - the pool and gardens and hammocks and olive groves and flowers and herbs.... We loved, too, that it is … see more
Very clean and pleasant apartment

The apartment is very clean, the kitchen equipment is brand new. Even the owner changed both the TV's, so we could watch the European Football Championship. Veronica very kindly meet us late in the evening and drove us from the parking lot to the a … see more

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